The Upperville Colt & Horse Show Returns

Upperville’s New Executive Director, Operations Manager, President, and Competitors Share What’s Coming for 2021 

Written by Victoria Peace

For many, the arrival of June in Middleburg means long summer rides through rolling green pastures, tailgating at twilight polo, and weekends spent visiting with friends at local wineries. However, it also marks the return of one of the area’s most time-honored and cherished events: The Upperville Colt and Horse Show. Founded in 1853 by Colonel Richard Henry Dulany, the Upperville Horse Show is the oldest horse show in the country. For more than 160 years, top-ranked equestrians and local competitors have competed side by side “under the oaks.”

Cancelled due to COVID-19 last year, this year’s show holds a special significance. “Just having the show this year is a cause for celebration,” Executive Director Emily Day said. 

People are anxiously awaiting the return of the excitement, camaraderie, sense of community, and appreciation of the Virginia countryside that attendees have enjoyed at Upperville for over a century and a half. 

For newly appointed Executive Director Emily Day, this will be her first experience at Upperville on the “official” side of the desk. In the past, she has always participated as a competitor. Coming from an extremely horse-oriented family, Day started riding when she was quite young. Her father was an equine veterinarian and her grandfather was Alexander Mackay-Smith, one of the founders of the National Sporting Library and Museum. Growing up, she would ride her pony unchaperoned around the countryside of her childhood home in Unionville, Pennsylvania before and after school. 

Jumping at Upperville Colt & Horse Show. Photo by Joanne Maisano.  

“It was a freedom that not many people get to experience at that age,” she said. She has always shown her horses in the jumper ring, and a photograph of her riding at Upperville in 2000 hangs in her office. Nowadays, one of her greatest passions is retraining retired Thoroughbred racehorses to show and foxhunt. “It’s been fun to follow the Retired Racehorse Project and watch something I’ve been doing most of my adult life get so popular with a new generation,” she said.

This year, she is extremely excited that Upperville will be offering a new Thoroughbred Incentive High Point Awards Program. As part of the program, the top three registered Thoroughbreds in four open divisions will receive prize money. 

“The idea is to give Thoroughbred owners an incentive to go on and show their talented horses in open divisions once they are ready to graduate from the breed-restricted classes,” Day said. 

As a former breeder and trainer of racehorses herself, Day hopes this will encourage more Thoroughbred riders to give the bigger, rated classes a try. There’s no doubt in her mind that as more members of the breed compete, more will return to the upper levels of big shows, emphasizing that “it would be great to see some more talented Thoroughbreds continue up the ranks” at Upperville. 

Other new offerings include the addition of another FEI Power and Speed Stakes class. Boasting $37,000 in prize money, the Power and Speed Stakes will kick off the other three FEI stakes classes offered at Upperville on Thursday, June 10 at 1 p.m.

And, that’s not all that competitors and spectators have to look forward to this year. There have been several upgrades to the show’s facilities, including a new lunging pad on the Grafton side of the show, modernized electric and water systems throughout the showgrounds, and updated NAARS footing in the Hunter 1 warm-up ring. 

But, perhaps the most exciting of all, is that many new trees and seedlings have been planted in and around the hunter rings, along the creek, and along the north edge of the property line. This effort ensures that future generations will be able to have the same amazing experience “under the oaks” that those who came before them did. “Our grandchildren will thank us!” Day said.

Evelyn, Sybil, and London. Photo by SAS Equine Photography.

Operations and Grounds Manager Tommy Lee Jones is responsible for implementing and overseeing many of these changes. Since 1982, Jones has tackled issues ranging from improving the drainage in the show rings to helping with the scheduling to ensure that the show runs smoothly. He emphasized that while making improvements to the showground, he is always mindful of protecting the special historic character that makes Upperville unique and “less commercial” than other shows. He loves the fact that “when you look across the road from the jumper side to the hunter side, it looks pretty much like it did many years ago.”

Upperville President Joe Fargis is also particularly proud of the recent work that has been done at the show to improve conditions for horses and competitors. Fargis is an Upperville veteran and has experienced almost all aspects of the show as a former competitor, judge, trainer, board member, and current president. He constantly reiterates that Upperville is a team effort and could not happen without “a dedicated group of people coming together for a common cause — a much-loved horse show.” 

When asked about his most memorable experience at Upperville, Fargis recalled a year when there was so much rain the week of the show that the mud was up to their knees. He remembered that “it was the muddiest horse show I’ve ever been to in my life, and yet the competitors still enjoyed it in spite of cars being stuck and horses covered in mud.” Something about the tough conditions instilled a sense of camaraderie in everyone at the showgrounds. 

When asked about her favorite Upperville memories, acclaimed local rider and trainer Sloane Coles talked about winning the family class, taking home ribbons in the local pony classes, and jumping her first Grand Prix at the show. She said that it felt like the whole crowd was behind her, cheering her on to jump a clear round. This was especially meaningful since Upperville is her “hometown” show. She grew up in The Plains and first competed in the show in the leadline division when she was around three years old. Since those days, Coles has continued to build a successful career as both a competitor and trainer, and has taken home prestigious titles at horse shows across the country. 

Gavin Moylan and daughters Evelyn and Sybil, alongside Tyler Beale with daughter London. Photographed by Shawna Simmons, SAS Equine Photography.

This year, she has clients in most of the classes at Upperville and will be showing some of her up-and-coming horses up to 1.40 meters. Unfortunately, her current Grand Prix horse is injured, but she hasn’t ruled out entering yet she is currently looking for another horse to compete on. One of her favorite things about Upperville is that it is able to seamlessly integrate its rich and historic past with modern facilities and the highest levels of competition, making it one of the best horse shows in the country. After having to miss it last year, she’s “looking forward to having it back.”

Local trainer Denice DeRisio Perry is also excited about the Upperville’s return this year because “the quality of the competition is of the highest standard.” The owner of Skyland Farm, a multi-faceted hunter-jumper show stable in Middleburg, Perry will have horses and riders competing in a variety of classes across both the hunter and jumper rings. She credits Joe Fargis, past presidents, and the Upperville board for going above and beyond to keep a locally run show up to a world-class level. This year, she hopes that the show is “blessed with good weather because there is not a more aesthetically pleasing showground in the country.”

Charlie McCann has been the Ringmaster of the hunter ring at Upperville for the past five years. He said one of his favorite parts of the job is getting to watch the top riders and horses come together from all over the country to compete in such a unique setting. It can be a hectic job, and on some days, it’s not uncommon to be working from eight in the morning until eight at night. But, he is quick to emphasize how much he enjoys the work. 

Under the oaks at Upperville Colt & Horse Show. Photo by Joanne Maisano.

McCann hopes to encourage first-time spectators to observe the hunter classes. Fans that are new to the sport often bypass the hunter rings because of the idea that all of the trips look more or less the same. However, McCann pointed out how gratifying and exciting it can be to learn to look deeper and really understand what the judges are searching for in terms of presentation, flow, and timing. He hopes that people will be encouraged to stop by and learn more about the hunters this year, adding that “it’s a lot of fun to watch.”

Last but not least, it would be remiss not to highlight some of Upperville’s smallest (and cutest) competitors. Featured on the cover, London Beale, Evelyn Moylan, and Sybil Moylan will all be showing in Upperville’s leadline division this year. London Beale will be turning three the week before Upperville. According to her father Tyler, while she doesn’t have an extensive riding resume yet, she did spend her winter in Wellington cantering poles aboard her mother’s top mount, Don Loma, to get ready for the leadline class. Tyler has “zero doubts she’s heading in her mother’s footsteps to be in the Grand Prix ring in no time with her early love of horses shining through strong.” Tyler and her mother Lindsay are “so excited to cheer on London this year in the best leadline class in the country.” 

Evelyn and Sybil Moylan have been travelling to horse shows since birth — for their family, horses are both a passion and a livelihood. Their father, Gavin, explained that during visits to the barn, both girls like to walk down the aisle feeding carrots and talking to the horses. They know all of the horses’ names, which stall they go in, who rides them, and they even help perform night check sometimes. For Evelyn and Sybil, one of their favorite parts of competing at Upperville is seeing their friends and family at the show. 

“Evelyn almost always has a loving cheering section when she goes in the ring, and she always asks who will be watching her compete, as it gives her confidence and makes it fun,” Gavin said. 

Alden Moylan, Sybil and Evelyn’s mother, emphasized that “we could not think of a more special place to begin one’s showing career than under the oaks at Upperville. Few shows are left in the U.S. that give you the butterflies as you ride across the gorgeous, historic grounds.”

Tyler and Alden both hope that as their girls grow older, they will find it just as special as they do.

This year, the show will be held from June 7 to June 13. Due to COVID-19, the show is operating based on CDC, USEF, and the Commonwealth of Virginia Health Department, and it is still uncertain whether spectators will be allowed to attend. The most up-to-date information on the situation can be found on the Upperville website. 

If spectators are allowed at the show, General Admission parking will be free. Day hopes this will encourage people to stop in and visit the show, enjoy the competition, and shop with Upperville’s vendors. 

“If those who are new to the community, or have given the show a miss in the past can use this opportunity to come see what the show is all about, we have no doubt new fans will emerge,” she said. ML

Follow the latest updates at upperville.com. Published in the May 2021 issue of Middleburg Life.